$1,653,039Average Value$1,215Average Price per Sq Ft62Homes For Sale
History and contemporary culture collide in Old Town
Old Town is at the heart of Key West in more ways than one. This centrally located historic district serves as the city’s main shopping, dining and entertainment hub, home to boutiques, local businesses and a bubbly nightlife scene on Duval Street. Roosters and chickens, thought to be brought over from Cuba in the 1800s, roam the streets like squirrels in suburbia, catching the attention of tourists. For locals, though, they’re just part of the island’s charm and have become somewhat of an unofficial city mascot.
As the southernmost island in the U.S., Key West is beloved by many for its clear, turquoise waters reminiscent of the Caribbean Sea. “The ocean is a big draw, and it always has been. A lot of people who buy homes here enjoy the water in one way or another. They’ll have a boat or go out on the charters,” says Key West resident Lisa Lennon, a Realtor with Berkshire Hathaway HomeServices Knight & Gardner Realty. Charter boats take off from the historic seaport area, which is also home to the city's aquarium and maritime museums. Boat owners can dock at nearby Garrison Bight Marina or join the Key West Yacht Club.
Old Town tells the city’s story through historic sites like the 1848 Key West Lighthouse and the 1852 Basilica of St. Mary Star of the Sea, one of South Florida’s oldest Catholic parishes. Visitors come from all over the world to stay at one of Old Town’s many vacation rental properties, and residents may find themselves navigating around large groups of tourists during the island’s high season, December through April. But for those who call Key West home, whether for six months or the whole year, sharing the island lifestyle with visitors isn’t a burden. “There's a saying here that you might have seen on bumper stickers,” says Key West resident Mike Caron, a Realtor with Keller Williams Key West Compass Realty. “It’s called ‘One human family.’ And that’s basically what Key West is.”
Many small package and liquor stores can be found around Old Town.
The Key West Shell Warehouse is a great place in Old Town to grab some souvenirs.
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Bahama Village is known for its conch-style homes
Among Old Town’s historic homes is the Oldest House Museum, a traditional white Bahamian-style home built in 1829 that presents a perfectly preserved pocket of the island’s early years. Known locally as conch style, this architecture is typical across Old Town and stands out for its cozy front porches, wooden shutters and intricate trim. Nowhere is this style more prevalent than in the historic community of Bahama Village, a small pocket within Old Town where rows of conch homes have survived since the 1800s. “It’s now become the face of Key West,” Lennon says. Like many homes in the neighborhood, these properties sit on slightly raised platforms, which increase air circulation underneath to limit mold and water damage. Old Town is in the X-flood zone, meaning that its higher elevation makes it slightly less flood-prone than lower areas like Midtown. However, flood insurance and hurricane preparedness features like impact-resistant windows are highly recommended.
Homeowners in this historic district must maintain the home’s original exterior whenever possible. The Historic Architectural Review Commission reviews all renovation proposals. Interiors, however, are often fully updated with open floor plans and modern kitchens. Single-family homes priced under a million usually need significant repairs. Older renovated properties cost between $1 million and $2 million, while renovated three- and four-bedroom homes typically range from $2.5 million to $5 million. Select historic properties and larger homes licensed for transient rentals can top out around $8 million. To combat rising rent prices, the city is developing dedicated workforce housing units in Old Town, which Donnelly says are “so desperately needed here because the apartment situation for workers is so expensive.”
Old Town Key West offers sections with smaller homes many with wrap around porches.
The historic district of Key West is known as Old Town with many museums and historic landmarks.
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Snorkeling and swimming at Fort Zach Beach
Fort Zachary Taylor Historic State Park, home to one of the country’s largest pre-Civil War weapons collections, covers 54 acres at the island's tip. A rock jetty curls out into the ocean, protecting the famous white sand beach from the strongest cruise boat currents and offering ample room for snorkelers and scuba divers to explore the clear water. Picnic tables lie in the shade of towering Australian pine trees, offering a welcome respite from the sun. “The city tried to remove all the pines about 10 years ago because they’re not indigenous to the area. The community raised $100,000 and got an attorney to save the pines. Can you imagine this without any shade?” says Brenda Donnelly, broker and owner of Brenda Donnelly Real Estate and a 40-year resident of Key West. The state park requires a small admission fee, but many residents get annual passes.
The interactive Florida Keys Eco-Discovery Center marks the beginning of Truman Waterfront Park, a renovated 33-acre green space with a popular shaded playground and splash pad surrounded by landscaped lawns. The park hosts a weekly farmers market on Thursday afternoon and is a popular spot to watch the sunset away from the bustle of Mallory Square, which is known for its nightly sunset celebrations. In addition to a few pocket parks and playgrounds, residents can use the basketball court at Frederick Douglass Gym and the outdoor pool and playground at Martin Luther King Jr. Community Center.
The Key West Lighthouse stands tall in Old Town and serves as a museum today.
The Beach at ack Taylor Historic State Park is a great place to cool off.
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Dining in Hemingway’s footsteps at Blue Heaven
Most restaurants sit north of Truman Avenue, creating a walkable culinary web. There are plenty of spots to grab fried conch fritters or stone crab when it's in season, and more than a dozen bakeries and eateries claiming to serve the best Key lime pie or Cuban coffee. Old Town Tavern & Beer Garden offers a diverse menu of international dishes, from traditional shepherd’s pie to homemade banh mi sandwiches. The iconic Blue Heaven pairs eye-catching art and rustic outdoor seating with gourmet ingredients and one of the tallest toasted meringue toppings available on a Key lime pie in the city. Before it was a restaurant, the property hosted boxing matches refereed by Ernest Hemingway himself. Now, diners enjoy live music and happy hour in a tropical setting complete with island wildlife. “Talk about chickens,” Caron says. “They run right through while you’re eating.” Other local recommendations include Santiago’s Bodega, an upscale tapas spot with homemade sangria, and Moondog Café, a colorful, mural-filled bakery across the street from the historic Hemingway Home and Museum.
When the sun sets, Duval Street comes to life with a diverse sampling of music carried on the breeze between bars. Jazz clubs offer weekly swing dancing lessons; rounds of beer fly at Sloppy Joe’s Bar, one of Hemingway’s hangouts; connoisseurs sip from their glasses at wine bars like Vinos on Duval. When the sun rises, longstanding markets such as Fausto’s Food Palace, a family-owned staple since the 1920s, fulfill gourmet grocery needs. Larger stores like Publix and retailers like T.J. Maxx and Ross Dress for Less are about 3 miles north in New Town.
Blue Heaven serves breakfast, lunch and dinner with live music from 10-2 and 4 to close.
Six toed cats can be spotted in the Hemingway House Museum in old Town Key West.
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Local troupes perform at the Red Barn Theatre
With everything from studio galleries to museums, Old Town is the beating heart of art and culture in Key West. Local troupes practice and perform at the Red Barn Theatre, housed in a historic red brick carriage house from the late 1820s. As one of Florida’s oldest professional theaters, its stage has been graced by Tennessee Williams, Shel Silverstein and Tony Roberts. The Key West Theater hosts acts from around the globe, while the Tropic Cinema highlights independent and international films under its Art Deco marquee. While some museums mainly attract tourists, others, like the Key West Museum of Art & History at the Custom House, welcome neighbors for happy hours, bingo nights and special speakers hosted by the city’s Art and Historical Society. Plus, many museums offer free or discounted admission to locals on select days.
Old Town is littered with historic buildings such as the Strand Theater.
Many bars and restaurants in Old Town have live music to entertain their guests.
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Island traditions include Hemingway Days, Key Lime Festival
Key West stays busy no matter the season, beginning the year with live music at the Mile 0 Fest and rounding out each December with a New Year’s Eve party at Mallory Square. In spring, Taste of Key West celebrates the city’s vibrant food culture. Come summer, locals look forward to the annual Key Lime Festival, which often coincides with the Fourth of July celebration and fireworks at Indigenous Park. Lobsterfest and Rum Fest are also summer highlights. But nothing compares to the turnout for Hemingway Days, a weeklong festival in July celebrating the famed author and late resident with lookalike contests, fishing challenges, street fairs and more. Fall brings the city’s renowned film fest and the annual Fantasy Fest, known for its energetic costume parties.
Key West High partners with the local college
Horace O’Bryant School, rated B on Niche, serves kindergarten through eighth grade students. Sections of the neighborhood are zoned for B-rated Gerald Adams Elementary School, about 4 miles away on Stock Island, but Monroe County’s choice enrollment system allows students to apply to any district school. B-plus-rated Key West High School offers dual enrollment courses with The College of the Florida Keys. The college also runs its own STEM-focused Academy Public Charter High School. Private schools in the area include Montessori Children’s School of Key West, which serves kindergarten through sixth grade, and The Basilica School of Saint Mary Star of the Sea, which recently reopened its high school program.
Key West High School is home to the fighting Conchs.
Gerald Adams Elementary Schools offers primary learning to students in the area.
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Old Town is pedestrian and bike-friendly
Old Town is a comfortable community for pedestrians and cyclists, with wide sidewalks, slow-moving traffic and ample bike racks. Car speed limits are low, especially on busy roads like Duval. But at 2 miles wide, the neighborhood is quick and easy to navigate. The Lower Keys Shuttle provides bus service throughout the city and offers routes to Marathon, 50 miles north. Key West International Airport is about 3 miles up the oceanside coast of the island.
Duval Street is the popular main street in Old Town with plenty of bars, eateries and retail.
Older homes built in the early 1900s are still prevalent around Old Town and Key West.
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Old Town Demographics and Home Trends
On average, homes in Old Town, Key West sell after 108 days on the market compared to the national average of 55 days. The median sale price for homes in Old Town, Key West over the last 12 months is $1,352,500, up 2% from the median home sale price over the previous 12 months.
Awarded the Florida Keys Preservation Star, this meticulously restored single-family home offers an enchanting blend of historic Key West charm, modern luxury, and high-yield investment potential. Holding a coveted TRANSIENT LICENSE allowing profitable nightly rentals, this turnkey Old Town sanctuary sits just a half-block from world-famous Duval Street while enjoying a prime position near
Grinnell Street is often said to be one of the best streets to live on in Old Town, and this charming 2-bedroom home makes it easy to see why. Tucked away in a small, quiet association of just seven residences, the property offers a peaceful setting right in the heart of Old Town, Key West.Inside, the home is bright and beautifully updated, with plenty of natural light throughout. The kitchen
NEW LISTING IN OLD TOWN WITH OFF STREET PARKING! This Old Town investment property comes fully furnished so you can move right in or start renting immediately. It is a legal DUPLEX with two units, each having one bedroom and one and a half bathrooms. Located on a fenced corner lot in Old Town, it's just blocks from Duval Street, making it very convenient for dining, shopping, nightlife and
Built in 2008, this stunning 3-bedroom, 3.5-bath pool home perfectly blends the timeless character of classic Key West architecture with the comfort and convenience of modern construction. Ideally located just a short stroll from shops, restaurants, bars, and the world-famous Duval Street, this home offers the best of island living. Step inside to a bright, open-concept main living space with a
Top floor unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit offers one of the most beautiful Key West Sunsets at the resort.The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row views as Coast Guard vessels and iconic pirate
Experience deeded ownership of the same week, each year (Week 45) at the highly desirable Galleon Resort with this premier timeshare opportunity. This unit showcases a wonderful location and some of the most spectacular sunsets in all of Key West.Filled with natural light, the residence also features a private balcony perfectly positioned to capture the stunning waterfront scenery above the
Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted Building C at the Galleon Resort. This PENTHOUSE, end-corner unit offers one of the most desirable locations in the resort, featuring unobstructed, straight-on views of the Gulf of Mexico. The residence boasts soaring vaulted ceilings, additional windows for abundant natural light, and multiple
Penthouse, top floor, end unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit delivers a truly unforgettable Key West sunset experience, among the finest views in Key West. The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row
Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await from this desirable 3rd-floor lock door unit - where 2 units can be combined into one or separate. Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove Café--everything you need for a
Experience deeded ownership of the same week each year (Week 22) at the highly desirable Galleon Resort. This timeshare offers a fantastic location and some of the most spectacular sunsets in Key West.Filled with light, the unit features a private balcony overlooking the Gulf and Marina. Enjoy views of passing sails and evening cruises, along with warm Gulf breezes and live acoustic music
Top floor Penthouse end unit! Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted building at the Galleon Resort. This unit offers one of the most beautiful Key West Sunsets at the resort.The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row views as Coast Guard
Experience elevated waterfront ownership with this deeded timeshare in the highly desirable Building C at the Galleon Resort. This penthouse end-corner unit boasts one of the most sought-after spots in the resort, showcasing unobstructed, head-on views of the Gulf of Mexico.The residence features vaulted ceilings, extra windows for enhanced natural light, and multiple balconies designed to
Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await from this desirable 3rd-floor lockout unit deeded timeshare week 46- where 2 units can be combined into one or separate. Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove
Location, Location, Location! A renovation project that will increase the value of your investment exponentially! This home is located between the Southernmost Point and the Hemingway House in the world-renowned City of Key West Florida. Besides the excellent location, this home has concrete fences, a concrete gated entry from Whitehead Street, a nice sized rear deck/patio, front sitting/garden
PENTHOUSE! Beautiful straight-on views of the Gulf, Pool, Beach, Sunsets, and Tiki Bar. Enjoy week 32 in this Timeless Timeshare and celebrate Lobster Week and the Rum Festival. The Galleon resort has Elevators, a rooftop deck, a gated parking garage, a sauna, an exercise room, and the Pirates Cove Cafe and Outdoor gas grills, which are located on the Marina side of the Galleon. Stay or rent it
Discover your place in the heart of Key West's most historic and vibrant neighborhood. The Lofts at Bahama Village offers affordable housing options designed for locals, where homeownership and rental opportunities meet the warmth of a close-knit community.Live steps away from iconic Key West landmarks, while enjoying the charm and cultural heritage that make Bahama Village truly one of a
The advertised rate of $19,161/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 21, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
The advertised rate of $6,690/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 17, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
The advertised rate of $11,220/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 3, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
Available now through March 31, 2027Enjoy Old Town Key West living in this charming 1 bedroom, 1 bathroom apartment at 624 Elizabeth Street. This bright and airy home features an open concept living room and kitchen with soaring high ceilings, creating a spacious and inviting atmosphere. A washer and dryer are conveniently located inside the unit for your everyday comfort.Rent is
Newly Renovated, furnished Townhome in Prime Old Town Key West located just 3 blocks from the beach! Experience the best of island living in this beautifully renovated 2-bedroom, 1.5-bath end-unit townhouse, perfectly situated in one of Key West's most sought-after neighborhoods. Features include a stunning new kitchen with quartz countertops, custom cabinetry, stainless steel appliances, and a
Offered for yearly rental in one of Key West's most iconic and desirable neighborhoods. This charming two-story townhouse features 2 bedrooms and 2½ bathrooms, storage attic, along with a welcoming front porch perfect for enjoying the relaxed island lifestyle. Located in a quiet Old Town residential neighborhood, the property is surrounded by Key West's history, character, and timeless charm.
Lovely furnished upstairs loft style apartment near Bayview Park in Key West! NO PETS or smoking! Private full size W/D, large walk in tiled shower, covered decks for tree top living! This is a very clean and well appointed apartment available for professional or military personal! Fenced, landscaped, and private! First, last, and security to move in. Rent includes ALL utilities! Please contact
Located in the heart of Old Town Key West! Walk, bike or drive your golf cart to famous restaurants, bars, tourist attractions and beaches. This 2 bedroom 2.5 bath home is being rented annually, fully furnished and includes two of street parking spaces, a rare find in Old Town! OWNER PAYS trash. One small dog is allowed upon approval by the owner and for a non-refundable pet fee. This is a
Jessica PrescottCoastal Collection Real Estate Inc.
Welcome to this great Old Town Location, a charming 1 bed / 1 bath apartment nestled in the heart of Key West. This cozy and well-maintained home offers a convenient and desirable location. Step inside and discover a thoughtfully designed living space that includes a stove, refrigerator, AC Mini Splits, washer/dryer, microwave, and a private deck. With its prime location, you'll have easy access
Super Cute 2 bed 1 bath downstairs apartment In Old Town Key West.At Historic Key West Annual Rentals, we strive to provide an experience that is cost-effective and convenient. That’s why we provide a Resident Benefits Package (RBP) to address common headaches for our residents. Our program handles pest control, air filter changes, utility set up, credit building and more at a rate of
Newly Renovated 2 bed with 2.5 bath! Located in Key West, this furnished two-bedroom, two-and-a-half-bath home offers a renovated kitchen with new appliances and included cable. A full-size washer and dryer are provided for convenience. Please note there is no off-street parking. Ideal for those seeking an updated, move-in-ready residence in a central location. This is a 6 to 9 month rental with
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